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WO2023223229A1 - Résine de liaison améliorée - Google Patents

Résine de liaison améliorée Download PDF

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Publication number
WO2023223229A1
WO2023223229A1 PCT/IB2023/055068 IB2023055068W WO2023223229A1 WO 2023223229 A1 WO2023223229 A1 WO 2023223229A1 IB 2023055068 W IB2023055068 W IB 2023055068W WO 2023223229 A1 WO2023223229 A1 WO 2023223229A1
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WO
WIPO (PCT)
Prior art keywords
lignin
bonding resin
dry
polyamine
range
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IB2023/055068
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English (en)
Inventor
Ashar ZAFAR
Dimitri Areskogh
Huynh Tram Anh PHAM
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Stora Enso Oyj
Original Assignee
Stora Enso Oyj
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Stora Enso Oyj filed Critical Stora Enso Oyj
Priority to EP23807146.8A priority Critical patent/EP4526389A1/fr
Priority to CN202380041206.6A priority patent/CN119384478A/zh
Priority to US18/867,371 priority patent/US20250270405A1/en
Priority to CA3257112A priority patent/CA3257112A1/fr
Publication of WO2023223229A1 publication Critical patent/WO2023223229A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J197/00—Adhesives based on lignin-containing materials
    • C09J197/005—Lignin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/005—Lignin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
    • C09J177/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2497/00—Presence of lignin

Definitions

  • the present invention relates to a bonding resin useful for example in the manufacture of insulation, such as mineral wool insulation or glass wool insulation.
  • the invention also relates to a method for preparing the bonding resin and to the use thereof.
  • Bonding resins are useful in fabricating articles, because they are capable of consolidating non- or loosely- assembled matter. For example, bonding resins enable two or more surfaces to become united. In particular, bonding resin may be used to produce products comprising consolidated fibers.
  • Thermosetting bonding resins may be characterized by being transformed into insoluble and infusible materials by means of either heat or catalytic action. Examples of thermosetting bonding resins include a variety of phenolaldehyde, urea-aldehyde, melamine-aldehyde, and other condensationpolymerization materials like furane and polyurethane resins.
  • Bonding resins containing phenol-aldehyde, resorcinol-aldehyde, phenol/aldehyde/urea, phenol/melamine/aldehyde, and the like are used for the bonding of fibers, textiles, plastics, rubbers, and many other materials.
  • Phenol-formaldehyde type bonding resins provide suitable properties to the final products; however, environmental considerations have motivated the development of alternative binders.
  • One such alternative bonding resin is a carbohydrate-based binder derived from reacting a carbohydrate and a multiprotic acid, for example according to US2007/0027283 and W02009/019235.
  • Another alternative bonding resin is the esterification products of a polycarboxylic acid reacted with a polyol, for example according to US2005/0202224. Because these binders do not utilize formaldehyde as a reagent, they have been collectively referred to as formaldehyde-free binders.
  • Carbohydrate-based bonding resins are made of relatively inexpensive precursors and are derived mainly from renewable resources; however, these bonding resins may also require reaction conditions for curing that are substantially different from those conditions under which the traditional phenol-formaldehyde binder system cured. Therefore, replacement of phenolformaldehyde type binders with an existing alternative has not been readily achievable.
  • EP2566904 is directed to a binder formulation comprising the reaction products of a carbohydrate reactant and a polyamine and materials made therewith.
  • Lignin an aromatic polymer is a major constituent in e.g. wood, being the most abundant carbon source on Earth second only to cellulose.
  • lignin an aromatic polymer
  • it has attracted significant attention as a possible renewable substitute to primarily aromatic chemical precursors currently sourced from the petrochemical industry.
  • Lignin being a polyaromatic network has been extensively investigated as a suitable substitute for phenol during production of phenol-formaldehyde adhesives. These are used during manufacturing of laminate and structural wood products such as plywood, oriented strand board and fiberboard.
  • phenol which may be partially replaced by lignin, is reacted with formaldehyde in the presence of either basic or acidic catalyst to form a highly cross-linked aromatic resins termed novolacs (when utilizing acidic catalysts) or resoles (when utilizing basic catalysts).
  • novolacs when utilizing acidic catalysts
  • resoles when utilizing basic catalysts
  • a particular problem when preparing insulation products is to obtain an appropriate balance between dry strength and wet strength properties, which largely depend on the bonding resin used. If the insulation product is intended for use such that it is exposed to moisture or water, such as for outdoor use, it is essential to use a bonding resin that provides sufficient wet strength.
  • lignin when lignin is provided in the form of an aqueous solution comprising ammonia and/or organic base, the phenolic hydroxyl groups in the lignin structure are deprotonated and free to react with other components of a bonding resin. This improves the reactivity and performance of the binder. Therefore, providing the lignin in the form of an aqueous solution comprising ammonia and/or an organic base speeds up the reaction significantly and hence facilitates the curing of the bonding resin, when manufacturing for example mineral wool insulation or glass wool insulation.
  • lignin in the form an aqueous solution of lignin comprising ammonia and/or an organic base the risk of degrading for example glass wool and mineral wool fibers is minimized.
  • the present invention is thus directed to a bonding resin comprising a reaction product of a carbohydrate reactant, lignin and a polyamine, wherein the carbohydrate reactant is selected from monosaccharide, a disaccharide or an oligosaccharide and wherein the polyamine is a primary polyamine selected from a group consisting of a diamine, triamine, tetraamine and pentaamine, and wherein the polyamine is H2N-Q-NH2, wherein Q is C1-C10 alkyl, cycloalkyl, C1-C10 heteroalkyl, or cycloheteroalkyl, each of which is optionally substituted; and wherein the lignin is provided as a solution and wherein the weight ratio of the carbohydrate to the polyamine is in the range of from 1 :100 to 100:1 and wherein the weight ratio of the lignin to carbohydrate, calculated on the basis of dry lignin and dry carbohydrate, is between 1 :
  • the present invention is also directed to a fibrous insulation product comprising the bonding resin according to the present invention.
  • lignin embraces any kind of lignin, e.g. lignin originated from hardwood, softwood or annular plants.
  • the lignin is an alkaline lignin generated in e.g. the Kraft process.
  • the lignin has been purified or isolated before being used in the process according to the present invention.
  • the lignin may be isolated from black liquor and optionally be further purified before being used in the process according to the present invention.
  • the purification is typically such that the purity of the lignin is at least 90%, preferably at least 95%.
  • the lignin used according to the method of the present invention preferably contains less than 10%, preferably less than 5% impurities.
  • the lignin may then be separated from the black liquor by using the process disclosed in W02006031175.
  • the lignin may then be separated from the black liquor by using the process referred to as the LignoBoost process.
  • the lignin may be provided in the form of particles, such as particles having an average particle size of from 50 micrometers to 500 micrometers.
  • the lignin may also be provided in the form of agglomerates having an average diameter of from 0.01 to 10 mm, such as from 0.1 to 5 mm.
  • the reactivity of the lignin can be increased by modifying the lignin by glyoxylation, etherification, esterification, amination or any other method where lignin hydroxyl content or carboxylic content or amine content or thiol content is increased.
  • the lignin used according to the present invention is not modified chemically after its extraction from wood and isolation. More specifically, the lignin is preferably not subjected to oxidation after having been isolated from the Kraft process.
  • An aqueous solution of lignin comprising ammonia and/or an organic base can be prepared by methods known in the art, such as by mixing lignin and ammonia and/or organic base with water.
  • the pH of the aqueous solution of lignin comprising ammonia and/or an organic base is preferably in the range of from 8 to 14, more preferably in the range of from 9 to 11 or 10 to 11.
  • organic bases include amines, such as primary, secondary and tertiary amines and mixtures thereof.
  • the organic base is selected from the group consisting of methylamine, ethylamine, propylamine, butylamine, ethylenediamine, methanolamine, ethanolamine, aniline, cyclohexylamine, benzylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, dimethanolamine, diethanolamine, diphenylamine, phenylmethylamine, phenylethylamine, hexamethylenediamine, polyetheramine, dicyclohexylamine, piperazine, imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2- phenylimidazole, 2-methylimidazoline, 2-phenylimidazoline, trimethylamine, triethylamine, dimethylhexylamine, N-methylpiperazine, dimethylbenzylamine, aminomethyl propylamine
  • the total amount of ammonia and/or organic base in the aqueous solution is preferably in the range of from 0.1 wt-% to 20 wt-%, preferably 0.1 wt-% to 10 wt-%, of the total weight of the aqueous solution comprising water, lignin and ammonia and/or an organic base.
  • the amount of lignin in the aqueous solution of lignin comprising ammonia and/or an organic base is preferably from 1 wt-% to 60 wt-% of the solution, such as from 10 wt- % to 30 wt-% of the solution.
  • the aqueous solution of lignin comprising ammonia and/or an organic base comprises less than 1 wt-% alkali and less than 1 wt-% inorganic base. More preferably, the aqueous solution of lignin comprising ammonia and/or an organic base does not comprise alkali and does not comprise inorganic base.
  • the amount of lignin in the bonding resin is preferably from 5 wt-% to 50 wt- %, calculated as the dry weight of lignin and the total weight of the bonding resin.
  • a polyamine is an organic compound having two or more amine groups.
  • a primary polyamine is an organic compound having two or more primary amine groups (-NH2).
  • primary polyamine are those compounds which can be modified in situ or isomerize to generate a compound having two or more primary amine groups (-NH2).
  • the polyamine is a primary polyamine.
  • the polyamine used in the bonding resin according to the present invention may be a molecule having the formula of H2N-Q-NH2, wherein Q is an alkyl, cycloalkyl, heteroalkyl, or cycloheteroalkyl, each of which may be optionally substituted.
  • Q is an alkyl selected from a group consisting of C2-C24 alkyl.
  • Q is an alkyl selected from a group consisting of C2-C8 alkyl.
  • Q is an alkyl selected from a group consisting of C3-C7 alkyl.
  • Q is a Ce alkyl.
  • Q is selected from the group consisting of a cyclohexyl, cyclopentyl or cyclobutyl.
  • Q is a benzyl.
  • alkyl includes a chain of carbon atoms, which is optionally branched. It is to be further understood that alkyl is advantageously of limited length, including C1-C24, C1-C12, Ci-Cs, Ci-Ce, and C1-C4. It is appreciated herein that shorter alkyl, alkenyl, and/or alkynyl groups may add less hydrophilicity to the compound and accordingly will have different reactivity towards the carbohydrate reactant and solubility in a binder solution.
  • cycloalkyl includes a chain of carbon atoms, which is optionally branched, where at least a portion of the chain in cyclic. It is to be understood that cycloalkylalkyl is a subset of cycloalkyl. It is to be understood that cycloalkyl may be polycyclic. Illustrative cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, 2-methylcyclopropyl, cyclopentyleth-2-yl, adamantyl, and the like.
  • chain forming cycloalkyl is advantageously of limited length, including C3-C24, C3-C12, Cs-Cs, C3-C6, and Cs-Ce. It is appreciated herein that shorter alkyl chains forming cycloalkyl may add less lipophilicity to the compound and accordingly will have different behavior.
  • heteroalkyl includes a chain of atoms that includes both carbon and at least one heteroatom, and is optionally branched.
  • Illustrative heteroatoms include nitrogen, oxygen, and sulfur.
  • illustrative heteroatoms also include phosphorus, and selenium.
  • a heteroalkyl is a polyether.
  • cycloheteroalkyl including heterocyclyl and heterocycle, includes a chain of atoms that includes both carbon and at least one heteroatom, such as heteroalkyl, and is optionally branched, where at least a portion of the chain is cyclic.
  • Illustrative heteroatoms include nitrogen, oxygen, and sulfur.
  • illustrative heteroatoms also include phosphorus, and selenium.
  • Illustrative cycloheteroalkyl include, but are not limited to, tetrahydrofuryl, pyrrolidinyl, tetrahydropyranyl, piperidinyl, morpholinyl, piperazinyl, homopiperazinyl, quinuclidinyl, and the like.
  • optionally substituted includes the replacement of hydrogen atoms with other functional groups on the radical that is optionally substituted.
  • Such other functional groups illustratively include, but are not limited to, amino, hydroxyl, halo, thiol, alkyl, haloalkyl, heteroalkyl, aryl, arylalkyl, aryl heteroalkyl, nitro, sulfonic acids and derivatives thereof, carboxylic acids and derivatives thereof, and the like.
  • any of amino, hydroxyl, thiol, alkyl, haloalkyl, heteroalkyl, aryl, arylalkyl, arylheteroalkyl, and/or sulfonic acid is optionally substituted.
  • the polyamine is selected from a group consisting of a diamine, triamine, tetraamine, and pentamine.
  • the polyamine is a diamine selected from a group consisting of 1 ,6-diaminohexane, 1 ,5-diamino-2-methylpentane and 3-(Aminomethyl)-3,5,5- trimethylcyclohexan-1-amine.
  • the diamine is 1 ,6- diaminohexane.
  • the polyamine is a triamine selected from a group consisting of diethylenetriamine, 1 -piperazineethaneamine, and bis(hexamethylene)triamine.
  • the polyamine is a tetramine such as triethylenetetramine. In one embodiment, the polyamine is a pentamine, such as tetraethylenepentamine. In one embodiment, the primary polyamine is a polyether-polyamine. In one embodiment, the polyetherpolyamine is a diamine or a triamine.
  • the carbohydrate reactant is a monosaccharide, a disaccharide or an oligosaccharide. In one embodiment, the carbohydrate is a monosaccharide in its aldose or ketose form. In one embodiment, the carbohydrate may be a reducing sugar.
  • the carbohydrate reactant is selected from a group consisting of dextrose, xylose, fructose, dihydroxyacetone, and mixtures thereof.
  • the carbohydrate reactant is a disaccharide, such as sucrose, lactose or maltose.
  • the carbohydrate reactant is an oligosaccharide, such as chitosan.
  • the weight ratio of the carbohydrate to the polyamine is in the range of from 1 :100 to 100:1 , calculated on the basis of dry solids.
  • the weight ratio of the carbohydrate reactant to the polyamine is in the range of from 20:1 to 1 :20, and more preferably in the range of from 10:1 to 1 :10 or most preferably in the range of from 1 :5 to 5: 1 or in the range of from 1 :1.1 to 1.1 :1 , calculated on the basis of dry solids.
  • the weight ratio of the lignin to carbohydrate, calculated on the basis of dry lignin and dry carbohydrate, is between 100:1 and 1 :100, preferably in the range of 20:1 and 1 :20 and more preferably in the range of from 10:1 to 1 :10 or in the range of from 6:1 to 1 :1 , calculated on the basis of dry solids.
  • the weight ratio of the lignin to polyamine, calculated on the basis of dry lignin and dry carbohydrate, is between 100:1 and 1 :100, preferably in the range of 20:1 and 1 :20 and more preferably in the range of from 10:1 to 1 :10 or in the range of from 6:1 to 1 :1 , calculated on the basis of dry solids.
  • the solid content of the bonding resin before curing is preferably in the range of from 10 to 70%, such as in the range of from 15 to 50%.
  • the bonding resin may also comprise additives, such as urea, tannin, surfactants, dispersing agents and fillers.
  • the bonding resin may also comprise plasticizer.
  • the bonding resin does not comprise plasticizer.
  • plasticizer refers to an agent that, when added to lignin, makes the lignin softer and more flexible, to increase its plasticity by lowering the glass transition temperature (Tg) and improve its flow behavior. Examples of plasticizers include polyols, alkyl citrates, organic carbonates, phthalates, adipates, sebacates, maleates, benzoates, trimellitates and organophosphates.
  • Polyols include for example polyethylene glycols, polypropylene glycols, glycerol, diglycerol, polyglycerol, butanediol, sorbitol and polyvinyl alcohol.
  • Alkyl citrates include for example triethyl citrate, tributyl citrate, acetyl triethyl citrate and trimethyl citrate.
  • Organic carbonates include for example ethylene carbonate, propylene carbonate, glycerol carbonate and vinyl carbonate.
  • plasticizers include polyethylene glycol ethers, polyethers, hydrogenated sugars, triacetin and solvents used as coalescing agents like alcohol ethers.
  • the plasticizer is a polyol, such as a polyol selected from the group consisting of polyethylene glycols and polypropylene glycols.
  • the weight ratio between plasticizer and lignin, calculated on the basis of dry weight of each component is preferably from 0.1 :10 to 10:1.
  • the weight ratio between plasticizer (if present) and lignin, calculated on the basis of dry weight of each component is from 0.1 : 10 to 10: 10, such as from 1 : 10 to 5: 10.
  • the bonding resin may also comprise coupling agent. Coupling agents are for example silane-based coupling agents. In one embodiment, the bonding resin does not comprise coupling agent.
  • a filler and/or hardener can also be added to the bonding resin.
  • fillers and/or hardeners include limestone, cellulose, sodium carbonate, and starch.
  • the bonding resin does not comprise filler and/or hardener.
  • the bonding resin according to the present invention does not contain formaldehyde.
  • the bonding resin does not contain phenol.
  • the bonding resin according to the present invention does not contain basic catalyst. Further, it is preferred that a basic catalyst is not used in the production of the bonding resin according to the present invention.
  • epoxy-based cross-linker is not used in the bonding resin.
  • the fibrous material used according to the present invention is for example mineral fibers (glass fibers, slag wool fibers, and rock wool fibers), aramid fibers, ceramic fibers, metal fibers, carbon fibers, polyimide fibers, certain polyester fibers, and rayon fibers. Such fibers are substantially unaffected by exposure to temperatures above about 120 °C.
  • the insulating fibers are glass fibers.
  • the mineral fibers are present in an insulation product according to the present invention in the range from about 70% to about 99% by weight.
  • fibrous material comprises cellulosic fibers.
  • the cellulosic fibers may be wood shavings, sawdust, wood pulp, or ground wood.
  • the cellulosic fibers may be other natural fibers such as jute, flax, hemp, and straw.
  • binder solution is the solution of chemicals which can be substantially dehydrated to form an uncured bonding resin.
  • the bonding resin may be cured, uncured, or partially cured.
  • the composition of the uncured bonding resin is referred to as an uncured bonding resin.
  • An uncured bonding resin is a substantially dehydrated mixture of chemicals which can be cured to form a cured bonding resin.
  • Substantially dehydrated means that the solvent (typically water or a mixture thereof) used to make the binder solution is vaporized to the extent that the viscosity of the remaining material (comprising the binder reactants and solvent) is sufficiently high to create cohesion between the loosely assembled matter; thus, the remaining material is an uncured bonding resin.
  • the solvent is less than 65% of the total weight of the remaining material.
  • a substantially dehydrated bonding resin has a moisture content between about 5% and about 65% water by weight of total binder. In one embodiment, the solvent may be less than 50% of the total weight of the remaining material. In one embodiment, the solvent may be less than 35% of the total weight of the remaining material. In one embodiment, a substantially dehydrated bonding resin has between about 10% and about 35% water by weight of total bonding resin. In one embodiment, the solvent may comprise less than about 20% of the total weight of the remaining material.
  • the term cured bonding resin describes the polymeric product of curing the uncured bonding resin.
  • the cured bonding resin may have a characteristic brown to black color. While described as brown or black, another characteristic is that the binder tends to absorb light over a broad range of wavelengths.
  • the cured bonding resin is substantially insoluble. For example, the bonding resin is predominantly insoluble in water.
  • the uncured bonding resin provides sufficient binding capacity to consolidate fibers; however, the cured bonding resin imparts the robust, long-lasting durability and physical properties commonly associated with cross-linked polymers.
  • the bonding resin reactants described herein are soluble in water and the when combined in water, a binder solution is obtained.
  • a surfactant is included in the aqueous solution to increase the solubility or dispersability of one or more bonding resin reactants or additives.
  • a surfactant may be added to the aqueous binder solution to enhance the dispersibility of a particulate additive.
  • a surfactant is used to create an emulsion with a non-polar additive or binder reactant.
  • the binder solution comprises about 0.01 % to about 5% surfactant by weight based on the weight of the binder solution.
  • the binder solutions described herein can be applied to fibrous material (e.g., sprayed onto a mat or sprayed onto the fibers as they enter the forming region), during production of fibrous insulation products.
  • the binder solution Once the binder solution is in contact with the mineral fibers the residual heat from the mineral fibers (note that glass fibers for example are made from molten glass and thus contain residual heat) and the flow of air through and/or around the product will cause a portion of the water to evaporate from the binder solution.
  • Removing the water leaves the remaining components of the bonding resin on the fibers as a coating of viscous or semi-viscous high-solids mixture.
  • This coating of viscous or semi-viscous high-solids mixture functions as a bonding resin.
  • the mat has not been cured. In other words, the uncured bonding resin functions to bind the fibers in the mat.
  • the above described uncured bonding resins can be cured.
  • the process of manufacturing a cured insulation product may include a subsequent step in which heat is applied as to cause a chemical reaction in the uncured bonding resin.
  • the uncured insulation product may be transferred to a curing oven. In the curing oven the uncured insulation product is heated (e.g., from about 150 °C to about 320 °C), causing the bonding resin to cure.
  • the cured bonding resin is thus a formaldehyde-free, water-resistant bonding resin that binds the fibers of the fibrous insulation product together.
  • the drying and thermal curing may occur either sequentially, simultaneously, contemporaneously, or concurrently.
  • An uncured fiber product typically comprises about 3% to about 40% of dry binder solids (total uncured solids by weight). In one embodiment, the uncured fiber product comprises about 5% to about 25% of dry binder solids. In one embodiment, the uncured fiber product comprises about 50% to about 97% fibers by weight.
  • a cured bonding resin is the product of curing the bonding resin.
  • the term cured indicates that the bonding resin has been exposed to conditions that initiate a chemical change. Examples of these chemical changes may include, but are not limited to, (i) covalent bonding, (ii) hydrogen bonding of binder components, and (iii) chemically cross-linking the polymers and/or oligomers in the bonding resin. These changes may increase the bonding resin’s durability and solvent resistance as compared to the uncured bonding resin. Curing a bonding resin may result in the formation of a thermoset material. In addition, a cured bonding resin may result in an increase in adhesion between the matter in a collection as compared to an uncured bonding resin. Curing can be initiated by, for example, heat, microwave radiation, and/or conditions that initiate one or more of the chemical changes mentioned above.
  • a cure can be determined by the amount of water released above that which would occur from drying alone.
  • the techniques used to measure the amount of water released during drying as compared to when a bonding resin is cured, are well known in the art.
  • Lignin ammonia solution was prepared first by adding 211 g of powder lignin (solid content 95%, as determined with a laboratory infra-red moisture analyzer) and 685 g of water to a 1 L glass reactor at ambient temperature and stirred until the lignin was fully and evenly dispersed. Then, 104 g of 28- 30% ammonia solution was added to the lignin dispersion. The composition was stirred for 60 minutes to ensure complete dissolution of the lignin.
  • Lignin-ammonia solution with plasticizer was prepared by adding 211 g of powder lignin (solid content 95%, as determined with a laboratory infra-red moisture analyzer), 685 g of water and 50 g of PEG400 to a 1 L glass reactor at ambient temperature and stirred until the lignin was fully and evenly dispersed. Then, 104 g of 28-30% ammonia solution was added to the lignin dispersion. The composition was stirred for 60 minutes to ensure complete dissolution of the lignin.
  • a binder solution was, if necessary, diluted with water and combined with a 1% solution of 3-Aminopropyl trimethoxysilane (APTES) in water to obtain a final solution with a total concentration of 20-23% (total DS) and a concentration of APTES of 0.5%.
  • APTES 3-Aminopropyl trimethoxysilane
  • This binder was combined with spherical glass beads (Sibelco AbraVer®, average size 300 - 400 pm) and stirred thoroughly with a spatula to obtain a thick homogeneous paste with a binder-on-glass concentration of 4%.
  • This paste was transferred to a silicone mold consisting of 8 identical rectangular cavities with a length of 215 mm, width of 107 mm and thickness of 16 mm.
  • the paste was distributed egually in all 8 cavities and the silicone mold was transferred to an oven and subjected to heating at 200 °C for 60 min.
  • the mold was allowed to cool to room temperature and the 8 identical solid bars were separated from the mold and stored for further analysis.
  • the mechanical performance of the glass bars is measured as dry strength (strength of dry glass bars) and wet strength (strength of glass bars after conditioning in water at 80°C for 2h).
  • the glass bars were divided into two sets for dry and wet strength.
  • the samples for dry strength were analyzed as-is.
  • the samples for wet strength were analyzed immediately after conditioning in water at 80°C for 2h.
  • Weight of the samples before and after conditioning is obtained to measure the water uptake of the samples.
  • the strength is measured as follows; the dimensions of the glass bar is obtained with a caliper.
  • the glass bar is mounted on a 65 mm supporting fixture consisting of two anvils, equally spaced from the center point. An upper anvil is slowly lowered at the center point with a constant rate. Force at the fracture point of the specimen is recorded and using the dimensions of the bar, converted to strength at break.
  • HMDA hexamethylenediamine
  • the composition was heated at 50°C during 20 min to ensure complete dissolution of all components.
  • a solution consisting of 10 g dextrose, 10 g hexamethylenediamine (HMDA), 8.3 g ammonia solution (28-30% concentration) and 51.7 g water was prepared to obtain a binder with a dry solid of 28% and a carbohydratepolyamine ratio of 50:50 (based on weight).
  • a solution consisting of 5 g hexamethylenediamine (HMDA) in 5 g water was prepared to obtain a polyamine solution with a dry solid of 50%.
  • the polyamine solution was combined with 50 g of a lignin-ammonia-plasticizer solution to obtain a lignin-polyamine binder with a total dry solid of 25%.
  • the finished binder was used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • Component B lignin-ammonia-plasticizer solution
  • the finished binders were subsequently used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • Component A A solution of 10.5 g dextrose and 10.5 g hexamethylenediamine (HMDA) and 14 g water was prepared to obtain a carbohydrate-polyamine ratio of 50:50 (based on weight) and a dry solid of 60%. The composition was stirred during 20 min to ensure complete dissolution of all components. The final composition was designated as “Component A”.
  • Component B lignin-ammonia-plasticizer solution
  • the finished binders were subsequently used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • a series of carbohydrate-polyamine compositions with a carbohydratepolyamine ratio of 60:40 (based on dry weight) and a dry solid of 60% (based on dry weight) were prepared as follows:
  • Polyamine designated “I PDA” is 3-(Aminomethyl)-3,5,5-trimethylcyclohexan- 1-amine.
  • compositions 11.1 through 11 .5 were stirred during 20 min to ensure complete dissolution of all components.
  • Component A was used to prepare a final binder by combining with a lignin-ammonia- plasticizer solution (designated as “Component B”) in the following amounts:
  • the finished binders were subsequently used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • Polyamine designated “J-ED600” is O,O'-Bis(2-aminopropyl) polypropylene glycol-block-polyethylene glycol-block-polypropylene glycol derivative.
  • the polyamine designated as “TETA” is triethylenetetramine.
  • the compositions 12.1 through 12.4 were stirred during 20 min to ensure complete dissolution of all components.
  • Component A a lignin-ammonia-plasticizer solution
  • Component B a lignin-ammonia-plasticizer solution
  • the finished binders were subsequently used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • the obtained mechanical strengths (dry and wet) as well as the differences between those two (in percent, relative to dry strength) are tabulated below.
  • a negative difference indicates a drop in mechanical strength while a positive difference indicates an increase in mechanical strength.
  • Two mixed carbohydrate-polyamine composition with a total carbohydratepolyamine ratio of 70:30 (based on dry weight) a dry solid of 60% (based on dry weight) was prepared by combining the following:
  • Composition 12.1 was stirred at room temperature during 20 min to ensure complete dissolution of all components.
  • Composition 12.1 was heated at 50°C during 20 min to ensure complete dissolution of all components.
  • compositions were further used to prepare a final binder by combining with a lignin-ammonia-plasticizer solution (designated as “Component B”) in the following amounts:
  • the finished binders were subsequently used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • Two mixed carbohydrate-polyamine compositions with a total carbohydratepolyamine ratio of 60:40 (based on dry weight) a dry solid of 60% (based on dry weight) was prepared by combining the following:
  • Composition 14.1 was stirred at room temperature during 20 min to ensure complete dissolution of all components.
  • Composition 14.2 was heated at 50°C during 20 min to ensure complete dissolution of all components.
  • the compositions (designated as “Component A”) were further used to prepare a final binder by combining with a lignin-ammonia-plasticizer solution (designated as “Component B”) in the following amounts:
  • the finished binders were subsequently used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • a solution consisting of 17.5 g dextrose, 7.5 g hexamethylenediamine (HMDA), 10.4 g ammonia solution (28-30% concentration) and 64.6 g water was prepared to obtain a binder with a dry solid of 28% and a carbohydratepolyamine ratio of 70:30 (based on weight).
  • Component A The composition stirred during 20 min to ensure complete dissolution of all components. The final composition was designated as “Component A”.
  • Component B lignin-ammonia-plasticizer solution
  • the finished binders were subsequently used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • a solution consisting of 10 g dextrose, 15 g hexamethylenediamine (HMDA), 10.4 g ammonia solution (28-30% concentration) and 64.6 g water was prepared to obtain a binder with a dry solid of 28% and a carbohydratepolyamine ratio of 40:60 (based on weight).
  • Component A This solution was combined with a lignin-ammonia-plasticizer solution (designated as “Component B”) in the following amounts:
  • the finished binders were subsequently used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • the obtained mechanical strengths (dry and wet) as well as the differences between those two (in percent, relative to dry strength) are tabulated below.
  • a negative difference indicates a drop in mechanical strength while a positive difference indicates an increase in mechanical strength.
  • compositions designated “Component A” and “Component B” were combined with a lignin-ammonia-plasticizer solution (designated as “Component C”) in the following amounts:
  • the binder was immediately (within 1-2 minute) used for preparation and analysis of glass bars as described in Examples 3 and 4.
  • Component A A solution consisting of 60 g lignin-ammonia-plasticizer solution, 2.3g dextrose and 2.0 g maltose was prepared and stirred until completely dissolved. This solution was designated “Component A”.
  • compositions designated “Component A” and “Component B” were combined in the following amounts:
  • the binder was immediately (within 1-2 minute) used for preparation and analysis of glass bars as described in Examples 3 and 4.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Manufacturing & Machinery (AREA)

Abstract

La présente invention concerne une résine de liaison utile par exemple dans la fabrication d'une isolation, telle qu'une isolation de laine minérale ou une isolation de laine de verre. L'invention concerne également un procédé de préparation de la résine de liaison et son utilisation.
PCT/IB2023/055068 2022-05-19 2023-05-17 Résine de liaison améliorée Ceased WO2023223229A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP23807146.8A EP4526389A1 (fr) 2022-05-19 2023-05-17 Résine de liaison améliorée
CN202380041206.6A CN119384478A (zh) 2022-05-19 2023-05-17 改善的粘合树脂
US18/867,371 US20250270405A1 (en) 2022-05-19 2023-05-17 Bonding resin
CA3257112A CA3257112A1 (fr) 2022-05-19 2023-05-17 Résine de liaison améliorée

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE2230155A SE545922C2 (en) 2022-05-19 2022-05-19 Bonding resin comprising lignin
SE2230155-0 2022-05-19

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WO2023223229A1 true WO2023223229A1 (fr) 2023-11-23

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EP (1) EP4526389A1 (fr)
CN (1) CN119384478A (fr)
CA (1) CA3257112A1 (fr)
SE (1) SE545922C2 (fr)
WO (1) WO2023223229A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4357194A (en) * 1981-04-14 1982-11-02 John Stofko Steam bonding of solid lignocellulosic material
US20110263757A1 (en) * 2010-04-22 2011-10-27 Rand Charles J Durable thermoset binder compositions from 5-carbon reducing sugars and use as wood binders
US20120135152A1 (en) * 2010-11-30 2012-05-31 William Christopher Finch Stable reactive thermosetting formulations of reducing sugars and amines
US20160185967A1 (en) * 2014-12-30 2016-06-30 Georgia-Pacific Chemicals Llc Composite products containing a powdered binder and methods for making and using same
US20210214557A1 (en) * 2014-07-17 2021-07-15 Knauf Insulation, Sprl. Binder Compositions and Uses Thereof
US20220106508A1 (en) * 2018-10-05 2022-04-07 Rockwool International A/S Aqueous binder composition

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4357194A (en) * 1981-04-14 1982-11-02 John Stofko Steam bonding of solid lignocellulosic material
US20110263757A1 (en) * 2010-04-22 2011-10-27 Rand Charles J Durable thermoset binder compositions from 5-carbon reducing sugars and use as wood binders
US20120135152A1 (en) * 2010-11-30 2012-05-31 William Christopher Finch Stable reactive thermosetting formulations of reducing sugars and amines
US20210214557A1 (en) * 2014-07-17 2021-07-15 Knauf Insulation, Sprl. Binder Compositions and Uses Thereof
US20160185967A1 (en) * 2014-12-30 2016-06-30 Georgia-Pacific Chemicals Llc Composite products containing a powdered binder and methods for making and using same
US20220106508A1 (en) * 2018-10-05 2022-04-07 Rockwool International A/S Aqueous binder composition

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CA3257112A1 (fr) 2023-11-23
SE545922C2 (en) 2024-03-12
SE2230155A1 (en) 2023-11-20
EP4526389A1 (fr) 2025-03-26
CN119384478A (zh) 2025-01-28
US20250270405A1 (en) 2025-08-28

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